Prospective Dolly (foaled 1987 in Florida) is a Thoroughbred racehorse who is best known as a three-time winner of two stakes races.
At age two in 1989 the filly won the Ontario Debutante Stakes at Fort Erie Racetrack in Fort Erie, Ontario and the My Dear Stakes at Woodbine Racetrack in Toronto.
At age three, Prospective Dolly's best stakes results were second-place finishes in the Miss Woodford Handicap at Monmouth Park Racetrack in New Jersey and the Star Shoot Stakes at Woodbine.
As a four-year-old in 1991, Prospective Dolly won the first of her three Whimsical and Seaway Stakes at Woodbine.
After retiring from racing, Prospective Dolly stood as a broodmare who produced seven foals.